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Vice President of Sales, Caliber

New England region

 

VP of Sales

Caliber Services Management

ABOUT CALIBER SERVICES MANAGEMENT

At Caliber, we are site maintenance and infrastructure experts. We deliver scalable solutions tailored to what you need and where you need it. We guarantee that we will deliver quality results on budget and on time. No more surprises, just first-class partnership through proactive communication, top notch professionalism, and reliable service. Caliber takes care of your sites so you can take care of your business.

We’re growing rapidly and building the commercial engine to match. This role is central to that trajectory.

THE OPPORTUNITY

We’re hiring a VP of Sales to lead and grow Caliber’s new business engine across our national footprint. As we scale our site maintenance and infrastructure services business, we need a proven sales leader to build a best-in-class sales organization, expand our client base, and drive Caliber’s next phase of growth.

This is a senior leadership role for a proven sales executive who thrives in a high-growth environment and is passionate about both building teams and winning in the market.

WHAT YOU’LL OWN

Build & Lead a High-Performance Sales Team

• Recruit, develop, and retain A+ sales talent using documented hiring best practices and structured continuous recruitment

• Personally engage with critical client stakeholders to understand their evolving needs, resolve escalations with high empathy, and secure long-term partnerships

• Ensure every seller has a scorecard, published quotas, and defined KPIs

• Utilize a sales rep development framework to onboard new hires and drive self-sufficiency

• Conduct regular documented performance reviews and create individual development plans for each team member

• Drive team retention with a 90%+ target

Deliver Revenue & Margin Growth

• Achieve 100% of the annual new-business revenue plan at margin targets

• Drive 20%+ year-over-year growth in new client revenue across target verticals

• Build and convert a qualified enterprise pipeline of multi-site prospects — targeting [$XXM+] in qualified new-business pipeline in year one

• Meet service contract revenue and margin targets per the annual operating plan

• Execute on strategic expansion initiatives into new service lines, verticals, or markets

Own the Anchor Relationship

• Serve as Caliber’s senior point of contact at the executive level for our anchor national account. Drive scorecard performance above benchmark every quarter and protect the portfolio with zero churn.

Develop & Implement the Commercial Plan

• Leverage data-driven market intelligence on competitors, client segments, and industry trends

• Maintain industry presence via key client relationships, networking, and business associations

• Develop and publish a comprehensive Commercial Plan with clear annual and quarterly goals

• Partner with the executive team to build an annual Commercial Plan covering target verticals, prospects, growth initiatives, quotas, and resource allocation

Drive Sales Process Excellence

• Track and manage KPIs and sales funnels for every seller on a daily and weekly basis

• Ensure 100% CRM adoption and disciplined pipeline hygiene and forecasting across the sales team

• Spend a minimum of 50% of time in the field with the sales team and clients

• Complete People Performance Reviews every six months

• Leverage technology — including AI and BI tools — to enable key sales and management processes

WHAT SUCCESS LOOKS LIKE (YEAR ONE)

• 20%+ year-over-year new-business revenue growth

• A qualified [$XXM+] pipeline with multiple active enterprise opportunities and at least one signed multi-site win

• A top-graded team with clear KPIs, development plans, and a documented sales playbook in place

• 90%+ sales team retention

WHAT YOU’LL BRING

• Proven track record in prospecting, lead generation, consultative selling, negotiation, closing, and CRM utilization

• Experience selling into facility services, infrastructure, or multi-site service industries, with the ability to translate technical/service capabilities into a compelling, differentiated value proposition

• Trust-building, active listening, empathy, and the ability to deliver tailored solutions that foster long-term client loyalty

• Strong business acumen — sales analytics, time management, organizational skills, and familiarity with industry regulations

• Skilled at delegating, motivating, onboarding, training, and managing performance against KPIs and goals

• Creative and practical problem-solving for unique client, operational, and market challenges

ESSENTIAL ATTRIBUTES

• Integrity & Trustworthiness — honors commitments and builds credibility with clients and colleagues alike

• Positive Attitude & Resilience — navigates adversity with composure and determination

• Adaptability — evolves with new technologies, market opportunities, and client needs

• Professionalism — punctual, polished, and respectful in all interactions

• Initiative — proactively drives results and uncovers new opportunities without waiting to be directed

WHO THRIVES AT CALIBER

We hire for three things above all else: Drive, Leadership, and Business IQ. We move fast, we hold ourselves accountable, and we expect everyone — regardless of title — to be willing to get their hands dirty. If you’re looking for a seat in a slow-moving organization, this isn’t it. If you want to build something and own the results, you’ll fit right in.

COMPENSATION

Base salary: $200,000 – $225,000, depending on experience and market location, plus performance-based incentive compensation. Caliber Services Management determines pay based on the cost of labor across US geographic markets, scope of responsibility, and relevant experience.

Caliber Services Management is an equal opportunity employer.

 

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